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Cheap flights from Chicago Midway Airport to San José from $153

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to San José departing on 8/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to San José

Cheap round-trip flights

Frontier Logo
6:20 am - 12:31 pmMDW-SJO
7h 11m1 stop
Frontier Logo
1:53 pm - 10:08 amSJO-MDW
19h 15m1 stop
$355Frontier
Find Deal
Sat, Aug 9 - Sat, Aug 23
Logo
9:12 pm - 10:32 amMDW-SJO
14h 20m1 stop
Logo
11:27 am - 8:22 amSJO-MDW
19h 55m1 stop
$411
Find Deal
Thu, Aug 14 - Thu, Aug 21
Southwest Logo
6:15 am - 12:45 pmMDW-SJO
7h 30m1 stop
Southwest Logo
1:40 pm - 12:05 amSJO-MDW
9h 25m1 stop
$427Southwest
Find Deal
Tue, Aug 19 - Fri, Aug 22
Logo
9:12 pm - 10:32 amMDW-SJO
14h 20m1 stop
Logo
12:18 pm - 2:10 pmSJO-MDW
24h 52m2 stops
$430
Find Deal
Thu, Aug 14 - Thu, Aug 21
Southwest Logo
9:10 am - 6:55 pmMDW-SJO
10h 45m1 stop
Southwest Logo
8:50 am - 10:25 pmSJO-MDW
12h 35m2 stops
$431Southwest
Find Deal
Tue, Sep 16 - Tue, Sep 30
Southwest Logo
8:00 am - 8:30 pmMDW-SJO
12h 30m1 stop
Southwest Logo
2:15 pm - 10:10 pmSJO-MDW
7h 55m1 stop
$438Southwest
Find Deal
Sun, Nov 2 - Tue, Nov 11
Southwest Logo
9:25 am - 8:30 pmMDW-SJO
11h 05m2 stops
Southwest Logo
9:00 am - 10:35 pmSJO-MDW
13h 35m2 stops
$442Southwest
Find Deal
Sun, Nov 2 - Tue, Nov 11
Southwest Logo
11:15 am - 6:55 pmMDW-SJO
8h 40m1 stop
Southwest Logo
1:40 pm - 11:20 pmSJO-MDW
8h 40m1 stop
$452Southwest
Find Deal
Thu, Sep 18 - Tue, Sep 30
Southwest Logo
7:50 am - 6:55 pmMDW-SJO
12h 05m2 stops
Southwest Logo
8:50 am - 10:00 pmSJO-MDW
12h 10m2 stops
$456Southwest
Find Deal
Thu, Sep 18 - Thu, Sep 25
Frontier Logo
6:20 am - 12:31 pmMDW-SJO
7h 11m1 stop
Frontier Logo
1:47 pm - 1:47 pmSJO-MDW
23h 00m1 stop
$531Frontier
Find Deal
Sat, Aug 2 - Sat, Aug 9

Southwest flights from Chicago Midway Airport to San José, San José Province

Our best Southwest deals on Chicago Midway Airport to San José, San José Province flight tickets
Southwest
Aug 19
MDW6:15 amChicago Midway
7h 30m
1 stop
SJO12:45 pmSan José Juan Santamaria Intl
Aug 22
SJO1:40 pmSan José Juan Santamaria Intl
9h 25m
1 stop
MDW12:05 amChicago Midway
$427
Find similar
Southwest
Sep 16
MDW9:10 amChicago Midway
10h 45m
1 stop
SJO6:55 pmSan José Juan Santamaria Intl
Sep 30
SJO8:50 amSan José Juan Santamaria Intl
12h 35m
2 stops
MDW10:25 pmChicago Midway
$431
Find similar
Southwest
Nov 2
MDW8:00 amChicago Midway
12h 30m
1 stop
SJO8:30 pmSan José Juan Santamaria Intl
Nov 11
SJO2:15 pmSan José Juan Santamaria Intl
7h 55m
1 stop
MDW10:10 pmChicago Midway
$438
Find similar

Frontier flights from Chicago Midway Airport to San José, San José Province

Our best Frontier deals on Chicago Midway Airport to San José, San José Province flight tickets
Frontier
Aug 9
MDW6:20 amChicago Midway
7h 11m
1 stop
SJO12:31 pmSan José Juan Santamaria Intl
Aug 23
SJO1:53 pmSan José Juan Santamaria Intl
19h 15m
1 stop
MDW10:08 amChicago Midway
$355
Find similar
Frontier
Aug 2
MDW6:20 amChicago Midway
7h 11m
1 stop
SJO12:31 pmSan José Juan Santamaria Intl
Aug 9
SJO1:47 pmSan José Juan Santamaria Intl
23h 00m
1 stop
MDW1:47 pmChicago Midway
$531
Find similar

See travel insights to San José from

How to get the cheapest flight ticket from Chicago Midway Airport to San José, San José Province

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to San José, San José Province?

The month of August is, on average, the cheapest month to fly to San José, San José Province from Chicago Midway Airport, with most prices found around $552. If you’re not able to fly to San José, San José Province in August, then September is your next best option. Flight prices from Chicago Midway Airport to San José, San José Province during September average around $552.

What is the cheapest day to depart on your flight to San José, San José Province?

The cheapest day to depart from Chicago Midway Airport to San José, San José Province is on a Tuesday when prices can be found for as low as $581. The most expensive day to fly to San José, San José Province is Saturday, with ticket prices averaging around $817.

What is the cheapest time of day to depart on your flight to San José, San José Province?

In the evening is the cheapest time of day to fly from Chicago Midway Airport to San José, San José Province when you can find flight prices for as low as $453. Flying to San José, San José Province in the evening is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to San José, San José Province, so prices are often more expensive at around $768 per ticket.

When to book flights from Chicago Midway Airport to San José, San José Province

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José, San José Province according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José, San José Province (MDW to SJO) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José, San José Province

Best Price Found

$153

Fastest flight time

6h 45m

Direct flights

None

Airports in San José, San José Province

1 airport
The best one-way flight to San José, San José Province from Chicago Midway Airport in the past 72 hours is $153. The best round-trip flight deal from Chicago Midway Airport to San José, San José Province found on momondo in the last 72 hours is $355.
The fastest flight from Chicago Midway Airport to San José, San José Province takes 6h 45m
There are no direct flights from Chicago Midway Airport to San José, San José Province. Popular non-direct route for this connection is Chicago Midway Airport - San José Juan Santamaria Intl Airport.
There is 1 airport near San José, San José Province: San José Juan Santamaria Intl (SJO)
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  • How far is Chicago Midway to San José Juan Santamaria Intl by plane?

    A flight from Chicago Midway to San José Juan Santamaria Intl will travel around 2210.5 mi. Typically, this will take 7h 10m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    Prices for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José Juan Santamaria Intl Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • What documentation or ID do you need to fly to San José Juan Santamaria Intl Airport?

    The travel and health documents you'll need for your trip to San José Juan Santamaria Intl Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José Juan Santamaria Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago Midway Airport to San José, San José Province?

Best airlines flying from Chicago Midway Airport to San José, San José Province

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José, San José Province with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $477Free CancellationRating
8.0
4,238 reviews
Search Southwest flights
DeltaPriceFrom $544Free CancellationRating
8.0
7,958 reviews
Search Delta flights

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Manuel Antonio
Jacó
Alajuela
Monteverde
Heredia
Dominical
Santa Elena
Esterillos Este

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José?

Finding the right flight to San José from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San José quick and easy, saving you time and money.

Can I find flights from Chicago to San José with flexible booking policies on momondo?

All flight searches from Chicago to San José on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José?

momondo provides multiple filters to help you find the best flight to San José from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to San José right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to San José flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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